My Most Embarrassing Financial Failures

So this is embarrassing: I’ve been advising institutions and individuals about financial decisions for nearly three decades and yet I’ve failed many times to make good choices myself.

I want to share a list of my failures with you both so you can avoid them and as a commitment device, so I don’t keep failing (the same way). But, before I can do that, I needed to understand why just remembering them was so hard. If you can’t even remember a mistake, what’s to prevent you from repeating it?

Here’s what I found: First, cognitive dissonance made recall difficult: I like to think of myself as smart, savvy, skeptical and analytical (to a fault). How could I be those things and still make such noob mistakes? Next, I learned how my ego reacted by rationalizing these mistakes with some choice supportive bias. Finally, a little search on “inability to admit mistakes” returned “Narcissistic Personality Disorder”, so at least I have that going for me.

Luckily, my wife offered to help me recall my errors (we’re good to each other that way). In order to qualify as a bad decision for this article, it must have resulted from a faulty process, not that there was an unwanted outcome. That could be the result of bad luck. Other criteria include that the decision has cost us thousands and that it’s really embarrassing to share because I should know better. Here they are:

For years, I bought actively managed mutual funds. As a result, I paid much higher management fees, underperformed indexes and took too much risk because I wasn’t sufficiently diversified. I believed the marketing hype of manager skill and was greedy to outperform the market.

Also for years, I traded individual stocks thinking my superior research, statistical and charting skills would allow me to make lots of money. Most years, the best I could say for my results was that I could apply my losses to reduce my taxes. In both 1. and 2., over-confidence and confirmation bias kept me trying too long.

Similarly, I often delayed selling my employer’s stock, which I received as part of my compensation, when inattention resulted in a loss and loss-aversion kicked in to make things worse.

We suffered a painful loss in a start-up we invested in whose value went to zero in three months flat. We failed to ask for a business plan or financial statements, relying just on the halo effect of the lead investor’s endorsement.

On the other side of the balance sheet, I waited too long to refinance our mortgage when interest rates fell and set the wrong target interest rate for the transaction. (59% of borrowers make these errors, according to a recent study.) I was distracted by a demanding job and family obligations. This alleged quant didn’t even calculate the value of the refinance option before exercising it.

Every year that I chose a health insurance plan without first creating a detailed spreadsheet likely cost us big-time. These plans are deliberately complex (premiums, co-pays, co-insurance, separate doctor and drug deductibles and individual and lifetime out of pocket maximums) and not comparable to discourage analysis and encourage mistakes.

I realized recently that I had accumulated too much life and disability insurance. Of course, my insurance agent did not remind me to cut back as my circumstances changed. I was wasting money on premiums for policies I no longer needed as the result of my own inattention.

It’s not just the big decisions that I messed up. There are also little choices that occur frequently and whose effects add up over time. I’m thinking about all the times I paid full retail, bought a cheap appliance only to have it break down months later, or ignored my carefully crafted budget to maintain appearances or satisfy a craving.

Whew! I’m glad that’s over with!

There are some useful takeaways from this exercise. I’m more vulnerable to marketing than I’d like to admit. I need to try even harder to be skeptical of marketing claims and understand companies’ and people’s incentives. For big decisions, I just have to make the time to do the analysis required. I also need to build better habits for the many small decisions whose effects accumulate.

It’s your turn. Leave a comment with a poor decision you’ve made that readers can learn from. No need to use your real name…

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One thought on “My Most Embarrassing Financial Failures”

Some of my mistakes include making the decision to lease a new car instead of repairing our used car. Another would be paying finance charges to make monthly insurance payments with an interest rate higher than I was receiving on my savings acct.